Ladies Man
by Ghostfile
Summary: Oliver reflects on some important people in his life. He discovers he really is a Ladies Man but not in the traditional sense. Set during "Warrior"
1. A Glass of Scotch

Disclaimer: All characters in this story belong to their respective creators/writers/studio. I'm just borrowing them temporarily.

A/N: This is my first fanfic ever. Something about the last scene in 'Warrior' inspired me to do this character study of Oliver. I'm just taking a dip in the writing pool so chapters will be pretty short. Hope you like it.

A Glass of Scotch

Oliver stared at the bottle of scotch as he slowly drank from his glass. Drinking used to be an escape, a welcome numbness to suppress the pain and disappointment. Now he was handling it better, didn't have to crawl into a bottle, or several, to escape the unpleasantness in his life. The penthouse bar was always well stocked but he didn't have any plans to get smashed. He truly appreciated a good single malt every once in a while and tonight was such a night. As his body and mind relaxed with each slow sip his thoughts turned to what had transpired in the last couple of weeks.

He hadn't purposefully ignored it but at the same time he'd never given it much thought. Not until Vordigan targeted Lois, Chloe and Mia. When he joined the Brotherhood of Sion he willingly took his vows to accept no lovers, no allies, no disciples. It made perfect sense to eliminate distractions in order to hone his skills. He realized now it was also meant to keep members removed from human emotions and unswervingly loyal to the Brotherhood. He'd learned much in just a year under Vordigan's tutelage but he had no desire to become the man Vordigan was making him. A man of the Brotherhood may have been ruled by the darkest parts of his being, empty of mercy or remorse, but not Oliver Queen. Despite the darkness in his soul, he just cared too damn much. Given the significant number of women whose lives he'd breezed through he wasn't sure if it was irony or karma that the most important people in his life, the ones he cared about the most, were women.


	2. Laura Queen

Laura Queen

Taking another sip he looked over the bar at the picture of his family. His mother, Laura Queen had been the first true lady in his life. He'd been too young to understand at the time what an incredible person she was. She had been a woman of quiet strength, grace and courage. Though it still hurt to think how much he truly missed her, the intervening years and maturity allowed him to appreciate what she'd given him in the short time he'd had with her. She'd wanted the best for him but never in a way that spoiled him. She loved him unquestioningly because he was her son and she, his mother.

He mentally sighed as he stared out at the Metropolis night sky. After his parents' deaths his relationships with women had been less than stellar, certainly nothing that would have made his mom proud. He'd gotten along fine with his nanny but the female housekeepers, cooks, teachers, they were transitory figures -- part of the scenery of his childhood and teenage years. If his parents had lived he might have learned that men and women could have meaningful relationships built on love and respect, but the combination of wealth, good looks and a heart-wrenching childhood loss made Oliver Queen irresistible to the fairer sex - and he had taken advantage of it. He enjoyed female company in the way all men do because early on his only reason for spending time with women was sex.


	3. Tess Mercer

Tess Mercer

He slowly swallowed another mouthful of scotch, feeling the warmth of the alcohol spread throughout his body as thoughts of Mercy filled his mind. She was his first try at having a relationship based on something besides hormones. After all, she'd saved him and he'd saved her - but it wasn't enough. He hadn't yet learned how to open himself up to a woman. Being someone's hero at a moment in life hadn't been hard. No, the hard part was realizing in a real relationship he couldn't casually pass in and out of a woman's life, that commitment meant being there ALL THE TIME. It scared him shitless when the possibility had stared him in the face so he'd taken the coward's way out. He'd stupidly cheated on her and pushed her away because he didn't have the balls to be a real man.

When Mercy moved to Metropolis he wanted to show her he'd changed, that he was willing to risk his heart. He'd asked her out to dinner hoping she might want to rekindle old feelings. When he'd arrived at the mansion it seemed she had her own agenda. Their night out was replaced by a physical and verbal sparring match that ended in a moment when he'd admitted his fear; a moment when she'd let down her guard; a moment when they opened up to each other. For one night past hurts were forgotten, or so he thought. It ended with a snap of a jewelry case and Mercy had closed herself off for good. Now it was his turn to hurt. Whatever path she'd traveled had turned her into a guarded woman with a cold, calculating countenance. The Tess Mercer before him bore no resemblance to the lady he'd known years before.

"What happened to you?" he'd asked. "I grew up," she'd replied. As she walked away, he realized she wasn't the only one.


	4. Lois Lane

Lois Lane

He looked down at his empty glass and set it on the bar as he reflected on the only other significant romance of his life...Lois. He'd certainly felt some sort of chemistry at their first meeting. And she'd clearly been interested in him but not enough to give him anything more than a lousy tip and advice to "aim higher." Chuckling, he remembered her abrupt dismissal of him as an "errand boy to the rich and arrogant". When she came to apologize for her rudeness he tried as hard as he could to keep her off balance. Despite his charm and manipulation she'd managed to stay on her toes and keep him at arms length. As they spent more time together she'd challenged him to do more, be a better man. It seemed like she was THE woman who could make his life complete. It wasn't as if he'd been ready to propose but having her in his life had made him truly happy. Then reality came crashing down upon his joy once the extent of Lex's 33.1 project came to light. Regret didn't even come close to describing how heart-wrenching it had been for him to leave.

He'd been willing to give up happiness for the greater good once but when business took him back to Metropolis he thought fate might actually be cutting him a break. Maybe there was a chance for love with Lois. In the end his alter-ego had made a romantic relationship impossible. Lois couldn't share him with the world as long as he was the Green Arrow but she wanted to be his friend. That had been harder than breaking up. He'd never made the transition from lover to friend. It was difficult for him to read Lois' concern or friendly gestures as platonic when his own heart ached for something more. He'd made one last try at opening up to Lois, letting her know the depths of his emotions in the hope she loved him in equal measure. But her love had changed, she'd moved on to Clark and he was alone, again. It took a little more time but once he figured out that Lois' happiness, even with another man, could make him happy, he was able to let go of the heartache and embrace the friendship.


	5. Chloe Sullivan

Chloe Sullivan

He stepped down to his desk to open his email. Skimming the inbox he noticed just how many messages he had from Chloe. Chloe Sullivan...aka Watchtower. It was quite ironic that as a man known for keeping company with attractive women he'd never really put Chloe in that category. Yes, he realized she was beautiful when they'd first met but she wasn't the kind of girl who usually turned his head. After Clark's brief introduction the only reading he got off Chloe was that of a quiet, little reporter trying to break into the big leagues. When Chloe had shown up at his place ready to help rescue Bart his first thought was Clark had to be out of his mind. Then he'd practically been stunned speechless once he found out just how much she knew... about everything. She'd smoothly made a place for herself on the team guiding and watching everyone's backs during the Ridge Facility mission as if it she'd done it a thousand times. On that day Chloe Sullivan had revealed to him her own alter ego, snarky sidekick to a super powered alien and friend of heroes.

Later on it just seemed natural to enlist her help for an occasional hack into Luthercorp's top secret files. Even Victor, whose cybernetics made breaking into systems as simple as breathing, bowed down to Chloe's computer wizardry. Once he realized how far-reaching and convoluted Lex's 33.1 plans were he knew he had to expand the team. He was looking for someone who could keep a closer eye on 33.1 as well as keep the team on task, so he'd offered Chloe the position of Watchtower, full-time.

He'd spent lot of time considering the implications of actively recruiting her because the biggest hurdle wasn't Chloe, it was Clark. Clark and Chloe's friendship had years of history cemented by the hero and sidekick part of their lives. Clark was justifiably protective and possessive of his best friend, and yet, he'd sensed part of that dynamic was holding her back. As far as Clark was concerned keeping Chloe out of harm's way meant keeping her in the background of his superhero act, but she wasn't meant to blend in with the scenery. He was sure Chloe was more than capable of taking a lead role, and unlike Clark, he thought she deserved to make her own decisions. He'd been a bit nervous that she might not be ready to play a new part; but like him, she was fueled with a thirst for justice, and she answered the call.

"Watchtower is officially online. Let's get to work."

Standing next to her at Isis, he realized that statement announced to the world Chloe Sullivan was no longer anyone's sidekick. She'd become a full-fledged hero, one that he was happy to have on his side.

A/N: For those of you who've read my story I really appreciate it. I'm sticking to SV canon as much as possible and hope my interpretation is believable. It might be a few days before I post the next chapter but it is in the works. Like it or not, please comment or review. As a newbie writer I'd appreciate the input.


	6. Dinah Lance

Disclaimer: Smallville, the show, the characters, and TV universe, don't belong to me but I like to borrow now and then.

Dinah Lance

Logging out of his email he hit the remote that opened the door to the Green Arrow room. Watching the doors open he thought about the new bulletproof glass he'd put in after Dinah shattered the old doors. Dinah had come as something of a surprise. He hadn't run into women super villains in the hero business so he couldn't help but flirt a little when he saw her on the roof of the Daily Planet. She'd gone barb for barb with him from the start, rebuffing his attempt at flattery and effectively cutting down his arrows with her sonic cry.

Chloe hadn't been the only one left injured on the rooftop. When Clark came by to chew him out for putting Chloe in danger he was still dealing with his bruised ego. Objectively he shouldn't have felt bad about a foe getting the upper hand in a skirmish, but being so effectively shut down by a woman was a blow to his manhood. Later, when Lois asked about the fishnet-clad blonde on the balcony, he'd once again been unprepared to deal with Dinah's alter-ego, the Black Canary. Once she'd shattered the doors to the Green Arrow room his mindset quickly adapted. She went from female villain to just plain villain. Lucky for him, she eventually turned out to be one of the good guys.

Despite her initial reluctance to join the team, she'd more than proven herself worthy. He believed in equality between the genders, really, but he also believed in being a gentleman around women. That meant Oliver Queen treated women like ladies and Green Arrow swooped in to save women in need of saving. Dinah didn't fit into his neat little categories. Not that he didn't think Dinah deserved to be treated like a lady – she did – so naturally he flirted with her like any other attractive woman. She created a whole new category because he didn't have to protect or save her, not like he did with Mercy or Lois or Chloe. In the world of vigilante superheroes with its life-or-death stakes, Dinah was the first to show him that a woman could kick ass and take names just as well as, and sometimes even better than, a man.

A/N: Sorry, this update took a little while, both real-life and my desire for perfection, though I still fall short (sigh!), slowed me down. As I've mentioned before I'm using SV canon so there's nothing about a serious romance between Oliver and Dinah like in the DC comics. It's just my interpretation but if Chlollie is now officially part of the SV story I just can't see Dollie developing in the future. The next chapter will be about Mia, of course! Still trying to decide if I'll end it there so if you have an opinion please let me know what you think.

Thanks and hugs to all of you who've read, commented on or favorited this story.


	7. Mia Dearden

Mia Dearden

He gathered the Green Arrow gear he'd need for patrolling and his next workout. He had a full day of training planned for Mia tomorrow and now that she was aware of his vigilante hero side he could incorporate some new things into their training regimen.

Until Vordigan reappeared he hadn't really thought of her as his disciple, he honestly just wanted to help her out. Watching her pimp drag her off after her fight had really pissed him off. Like so many scumbags he used fear and intimidation to trap her, keep her feeling cowed and hopeless. He'd recognized a kindred spirit when he saw her in the ring, someone trying as hard as she could to escape from the darkness. She was a good fighter too, who, with the right training, could be great. She just needed a helping hand, and who was he to pass on an opportunity to be a woman's knight in shining armor?

As the car raced down the street he almost regretted letting her drive the Aston Martin but he needed her to see a sign of trust from him. When he'd made his pitch about helping her make a better life she'd been skeptical, even sarcastic about him being "her hero," but she'd listened. He'd been straight with her because anything else would have been a waste of time.

Mia represented a lot of firsts for him: training someone to become a better, smarter fighter; assuming a long-term responsibility for another human being as a mentor; dealing with emotional pain with something more fulfilling than alcohol and empty sex. And for the first time he looked, not at the woman, but at the person. Mia was the first attractive woman (okay, he was vain, but he was Oliver Queen) with whom he'd purposely started a platonic relationship. She was like... a kid sister. And, strangely enough, he found he rather enjoyed the role of older brother.

But, old habits die hard. When he suspected someone was targeting people close to him he did what he always did, he pushed those people away. It was for Mia's own protection of course, but it was already too late. Vordigan had her and he had to face off with his former mentor. He wasn't afraid to die at Vordigan's hand to protect the ones he cared about; no, it was the fear that the darkness within him would push him to kill that worried at his mind. He'd wrangled with that demon because of Lex so he was determined not to take Vordigan's life, but every wound inflicted on a loved one - first Lois, then Chloe, and finally Mia - took a toll on his soul and fed that inner darkness. A darkness he'd spent most of of his life trying to outrun.

But Mia wasn't running. Not from her own personal demons (and he was pretty sure she had her fair share)... or his.

She might be his student but she'd imparted some wisdom of her own. "There's a dark place inside of everyone, Oliver. What we do with it depends, not on who our teachers are, but what we do with the lessons learned." Despite all the things he thought he'd be teaching her, he realized he could stand to learn a lesson or two from her along the way.

**A/N**: This chapter gives the last commentary on each important lady's influence on Oliver (unless SV adds someone else to the mix). It's taken longer than I thought but I'm happy knowing people are enjoying the story. I plan on wrapping it up with a final summary of sorts but am trying to decide if I should go with a general statement or point one of his relationships in a new direction. Any thoughts?


	8. Of Disciples, Allies and Lovers

**Disclaimer**: All characters and story elements from Smallville remain the property of the creators, producers and CW. I'm not doing this for monetary gain, just want to have a little fun with characters I love.

Of Disciples, Allies and Lovers

After changing into a T-shirt and jeans, he checked to make sure his gear was properly packed. Looking up at the bar his gaze was drawn to the bottle of scotch. What the hell, he thought, and placed it carefully in the bag. If he'd intentionally set up a loyalty test to see just how dedicated Mia was, then she'd passed with flying colors. Despite everything he'd said and done she'd stuck it out; she showed him just how important their relationship was to her. It was startling to think a woman valued him enough to make a long term commitment. After Lois, he was grateful his Green Arrow persona hadn't changed how Mia perceived him. It wouldn't hurt to show he appreciated her loyalty. They could unwind a bit after practice and maybe he could teach her a few things about a good scotch.

Gear and scotch loaded up he headed down to the garage. It was a little too early to go out patrolling, so if he headed over to the warehouse now he could get in a little target practice.

Pulling out onto the street he felt his stomach grumble. He'd skipped dinner when his afternoon conference call had lasted well into evening, so food would definitely be a good idea. He wasn't making the headlines as billionaire playboy, Oliver Queen, but his alter ego seemed to have taken over the spot. It didn't matter what he did, he couldn't seem to stay out of the tabloids. He could just imagine what some errant criminal might be quoted as saying if his stomach rumbled while bagging said bad guy.

"Yeah, I was really scared when the Arrow dude showed up, until I heard his stomach making noises. Maybe he's really busy, but I still have time to grab a burger." Even as the Green Arrow, he had an image to maintain - and it didn't need to include speculation about being on a diet to maintain his figure.

As he drove he wondered if anyone would be interested in having a meal with him. In the not so distant past he'd frequently eaten dinner at the trendiest, most exclusive eateries, and he always had at least one gorgeous female companion. He was still eating out, but having returned to both CEO and hero duties, he usually found himself eating at the office or getting take out with his fellow heroes in arms. When exactly WAS the last time he'd been out for a nice dinner?

He supposed he could give Dinah a call if he wanted a female dinner companion. She'd dropped quite a few hints in her emails about getting together socially. He enjoyed the flirting; it was fun but harmless. But the idea of taking things to a different level left him feeling... uncomfortable.

The old Oliver Queen wouldn't have given it a second thought, but then his younger self never bothered to stick around for, much less consider, the consequences. At least he had been sensible enough not to date a secretary or a business consultant for Queen Industries. He had too many classmates with first-hand experience when the sordid details were published in tabloids, or worse still, a nasty lawsuit dragged a man's name and business through the mud. No, it would be too much like dating one of his employees. He couldn't be slapped with a sexual harassment suit, but everyone on the team would feel the repercussions. He still had to work with Dinah, and if things crashed and burned the team might too. He respected Diniah, and attractive as she was he just wasn't _attracted to_ _her_. Plus, he thought ruefully, if they did get romantically involved he'd probably unintentionally do something to truly piss her off, and unlike other women who would just throw a tantrum or slap him across the face, she'd just give him a straigtforward ass kicking.

Well, if a mildly flirtatious dinner was out he could swing by Watchtower and see how things were shaping up in Metropolis for the evening. It also wouldn't hurt to find out if there was anything new with the Kandorians. Chloe was probably waist deep in surveillance and information gathering activities. Maybe he could pry her away from her digital cocoon for a bite to eat. He really didn't feel like eating alone, and he'd bet his entire fortune Chloe had skipped at least one meal today. She might think she could subsist on her usual diet of liquid caffeine but she'd need a real meal to stay sharp. If Chloe were out he could set up a target and still get in a little archery practice.

Pulling a sharp u-turn at a clear intersection, Oliver dialed the number of Chloe's favorite Thai place as he changed course for Watchtower.

**A/N**: Yeah, it's been a long time since I've updated. I've got one last chapter to go and I'm struggling to get it just right. Sorry if this seems like a filler but it does lead up to something, I promise!

Thanks to Ironman 29758, olivess_09, batgirl2992, anacat, VoicesInTheWind, and Lady Belletrist for your reviews and suggestions. It feels great to know readers are interested enough in the story to comment.


	9. Target Practice

Target Practice

Thai food in hand, Oliver tried again to get a hold of Chloe, but there was still no answer at Watchtower. It wasn't an emergency so he really didn't want to call her cell. Probably just as well, he thought. She deserved a night out with Lois or hanging out in a coffee shop. He'd look through whatever status updates she had put together when he got there.

After parking his car he pulled out the gear bag, grabbed the food and headed to the elevator. He had a bow and arrows stored at Watchtower but the one in the bag was his favorite. Plus, if he got thirsty he had the scotch.

As the elevator security system confirmed his bio-print Oliver recalled what Chloe had said when she'd shown up at his penthouse the first time. "We trust each other. Clark tells me everything." While she and Clark were still friends they hadn't completely patched up the big rift created by Clark's departure after Jimmy's death. Of course, Clark couldn't be singled out for pulling a disappearing act on her; everyone had taken Jimmy's death hard. And everyone, except Chloe, had run away. Despite the superpowers and super skills, when reality came calling he and Clark had turned out to be the biggest cowards while Chloe turned out to be the true hero. He'd hoped he'd redeemed himself somewhat since Roulette. At least he wasn't at the top of Chloe's shit list. If Clark weren't keeping such a death-grip on that spot it might even be comical. Even with his X-ray vision Clark couldn't see how much he'd hurt Chloe when he left to do his alien walkabout. When Clark told Chloe he needed to purge his humanity he should have realized that saying he didn't want to be human meant he didn't want anything to do with her. As if losing a spouse wasn't tragic enough, having your oldest and best friend basically say you're irrelevant with a straight face must have been a crushing blow to her spirit. Chloe and Clark may have been the dynamic duo when he'd first met them, but now it seemed like he, not Clark, was the one Chloe came to when she had something to hash out. Sure he relied on her the way Clark did to help get the job done, but at least he had the decency to show some gratitude more than once a decade. Clark was an idiot for not seeing what was staring him right in the face, he thought, as the elevator doors opened.

There was no sign of Chloe as he stepped off the elevator. He set his gear by his desk and put away the food he'd gotten for her in the dorm fridge. If she didn't come back before he left Watchtower he'd leave a note to let her know there was food if she were hungry. Carrying his dinner over to the desk he turned on his computer work station and settled in to eat and read. As he pulled up different files his brain continued to muse over his partnership with Chloe. She'd made a huge save pulling him back into the hero game. If she hadn't cared so much he'd still be wallowing in guilt and self-pity. Hell, he'd probably be dead given how close he'd gotten to self-destruct. When he'd screwed up with Tess, (and hooking up with the hostess was minor compared to getting your friend's husband killed), she'd walked out on him. But Chloe, who was suffering the triple blows of losing her husband because of his mistakes, being frantic with worry over Lois being MIA, and dealing with complete rejection by her supposed best friend, reached out to help him – ungrateful, narcissistic, Oliver Queen – and showed him that his life was worth living. She'd called him a hero, but really the title belonged to Chloe. She wasn't just an unsung hero in their little band, she was his personal hero.

Closing out the files he looked around for a spot for a target. Not that he'd miss, but Chloe would kill him if he scratched any of the computer systems. He may have paid for them but the computers were without a doubt hers. Surveying the room he decided setting up the target near the door was the best spot. It gave him the longest distance for firing arrows and kept the electronics out of the line of fire. He threw away the take-out containers and pulled out his archery equipment.

Strange. Maybe it was being in Watchtower, but so many things in his life seemed to come back to Chloe. They worked together well, they both had a proactive view of how to make the world a better place, and they had the same focus when it came to reaching an objective. If he had to be honest, once Chloe assumed Watchtower duties full time the two of them were (practically inseparable) almost always in contact, more so than he'd been with any girlfriend. She was actually better than a girlfriend because he could talk to her about anything. He'd never worried about what to say with any of his casual dates because things never lasted any longer than a headline in the society pages. With Tess he'd kept her in the dark about his past bad decisions, but she'd been truly wounded by the part of him she didn't know and left because she wasn't equipped to handle it. For Lois it had been about protecting himself to keep her away from his alter ego, but when Dinah outed him so spectacularly, Lois was more outraged by the betrayal of trust than anything else. With Chloe he had nothing to hide, because she already knew everything. Really it was impossible for him to recall a day when he didn't email, call, or text her since she'd helped him get his life back together. Clark might no longer be telling her everything anymore, but he was only too happy to be sharing the trials and tribulations of his crazy life with Chloe.

Standing in Watchtower adjusting his bow Oliver Queen had an epiphany. Not since his mother had any woman done as much for him as Chloe; not Tess who'd saved his life, not Lois who'd given him honesty and friendship. Here was a smart, beautiful woman who was fully cognizant of the highs and lows of his life, who knew him not just as billionaire Oliver Queen or vigilante hero Green Arrow, but as plain old Oliver, and she **still** wanted him by her side. Granted, she wanted a partner in justice but really their compatibility extended beyond that of colleagues. Plenty of women had set their sights on him because of his fortune, looks, or both, but Chloe wanted him for entirely different reasons. She wasn't interested in him for herself; she was interested in him because she wanted him to be true to himself. Like Tess she'd saved his life and like Lois she didn't put up with his crap, but unlike either of them she chose to stick with him. She saw something no other woman had, the hero in his heart, as she'd called it. Was it possible the perfect woman had been right in front of him all along?

"Chloe," he said out loud.

He needed a drink, something to settle his thoughts, and luckily he'd brought just the thing. He quickly poured himself a double and took a slow sip. He'd never admit it out loud but Carter Hall was right, he was a jackass. A blind, jackass at that. For so long he thought having emotional attachments was a weakness but the birdman had made it quite clear that family and friends were a source of strength. The man Oliver would have picked as poster boy for brooding, isolated hermits in realty exemplified what it is to be a devoted friend and husband.

The slow burn of the scotch he swallowed fueled his thoughts as he considered what Chloe truly meant to him. He thought about his parents, what kind of relationship they had had and how devoted they were to each other. For the first time, okay second, in his life he wanted that too. As much as he'd loved Lois a relationship would never have worked out. He and Lois had been exactly like Chloe and Jimmy. Chloe's inability to share all parts of her life with Jimmy had placed a strain on their marriage that would probably have torn it apart even if Doomsday had never existed. If Lois hadn't been dramatically enlightened about his hero persona their relationship would have eventually disintegrated under the weight of his own secrets. But Chloe, she was different, unique. She was his friend, advisor, nursemaid, confidant, and, ultimately, savior. Chloe truly was the most important person in his life and now that he realized it he was damn well going to show her how much he appreciated her. If Carter could find a partner for eternity then maybe there was a chance for him and Chloe in this lifetime.

The real question though, was **he** the kind of man Chloe wanted to get involved with? Was he good enough for her?

Draining his glass, he set it on the table and picked up his bow. Convincing Chloe might very well be impossible but he was determined to try. All he needed was an opening, just the right moment to plant the idea of her with him.

Well, he'd brought up his gear to get in some target practice so he might as well get started. He fired an arrow to test the sights. Whizzing to the target it hit the red circle. Frowning, he adjusted the sight then fired another arrow. Arrow number two was closer than the first, but still not in the center. After a little more tweaking he notched a third arrow. He pulled back on the bowstring and released it – just as Chloe came in.

A/N Just looked through my files and realized I never posted this chapter. If anyone's still interested, please enjoy!


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